Naratriptan → Naratriptan hydrochloride

HRID 1028423Notes

Reaction equation

HRID 1028423 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)(=[O:5])=[O:4].CC(O)C.[ClH:28]>CC(C)=O>[ClH:28].[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 4440Naratriptan2×HCID 21912024Isopropanol hydrochloride

Product 1

HCID 60875Naratriptan hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
7.5 °C

Procedure

2-[3-(1-Methyl-piperidin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide i.e. (Naratriptan base) (100 gm) was dissolved in acetone (1000 ml) under stirring for 30 minutes to obtain a clear solution. The reaction mass was cooled to 5-10° C. and pH of the reaction mass was adjusted to 1.0 with 20% IPA-HCl solution. The temperature of the reaction mass was raised to 25° C. and filtered. The solid was dried in vacuum chamber at 50-55° C. to obtain the title compound. (Yield: 95 g, HPLC Purity: 99.56%)

Workup

  1. customto obtain a clear solution
  2. temperatureThe temperature of the reaction mass was raised to 25° C.
  3. filtrationfiltered
  4. customThe solid was dried in vacuum chamber at 50-55° C.

Sources & evidence

ORD record
ord-391f76714c5443b28bd4d0c2f346adac
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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